α-(benzyloxycarbonylamino)benzyl(methyl)phosphinic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-(benzyloxycarbonylamino)benzyl(methyl)phosphinic acid
• 英文别名: (α-(benzyloxycarbonylamino)benzyl)methylphosphinic acid；Methyl-[phenyl(phenylmethoxycarbonylamino)methyl]phosphinic acid；methyl-[phenyl(phenylmethoxycarbonylamino)methyl]phosphinic acid
• 化学式: C₁₆H₁₈NO₄P
• 分子量: 319.297
• InChiKey: YTIGDCMPARLKRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-(benzyloxycarbonylamino)benzyl(methyl)phosphinic acid 在 disodium hydrogenphosphate 、 Chiral AX QD-1 stationary phase 作用下， 以 甲醇 、 水 为溶剂， 生成 ((S)-Benzyloxycarbonylamino-phenyl-methyl)-methyl-phosphinic acid 、 ((R)-Benzyloxycarbonylamino-phenyl-methyl)-methyl-phosphinic acid
  参考文献：
  名称：

  High-performance liquid chromatographic enantiomer separation and determination of absolute configurations of phosphinic acid analogues of dipeptides and their α-aminophosphinic acid precursors

  摘要：

  The enantiomers of N-benzyloxycarbonyl-phospinic pseudodipeptides and their N-benzyloxycarbonyl-alpha-aminophosphinic acid precursors as well as various other structural analogues were separated oil a set of cinchona alkaloid-derived chiral anion-exchangers by HPLC in the reversed-phase mode. Semi-preparative scale chromatography provided single enantiomers in 100 mg quantities. The configurations of the enantiomers were assigned indirectly by enantioselective chromatography on the basis of the elution order and was confirmed by enantiomeric reference compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00537-8
• 作为产物：
  描述：

  甲基-次磷酸 、 dibenzyl (phenylmethylene)dicarbamate 在 乙酸酐 作用下， 以69%的产率得到α-(benzyloxycarbonylamino)benzyl(methyl)phosphinic acid
  参考文献：
  名称：

  氢磷酰基化合物的酰胺烷基化

  摘要：

  作为构建假α，α′-二肽分子的α-氨基磷酰基片段的简便方法，开发了一种新的温和的氢化磷酰基化合物在乙酸酐和乙酰氯混合物中的酰胺基烷基化的方法。反应中间体N，N′-亚苄基-和N，N检测，分离和鉴定了'-亚烷基双氨基甲酸酯。该报告提供了以下结果：研究了先前与双氨基甲酸酯合成的氢磷酰基化合物在乙酸酐和其他溶剂中的直接相互作用，磷组分和双甲酸氨基甲酸酯的结构的影响以及酸催化对该双组分反应过程的影响。 。提出了氢磷酰基化合物酰胺烷基烷基化三组分反应机理的新形式：它被认为是一个多阶段过程，涉及到双甲氨基甲酸酯的形成阶段，然后是Arbuzov型反应阶段，中间形成酰基亚胺基阳离子和具有三价磷的P-OAc衍生物。

  DOI：

  10.1134/s1070363211060041

文献信息

• Amidoalkylation of hydrophosphoryl compounds
  作者：M. E. Dmitriev、E. A. Rossinets、V. V. Ragulin

  DOI：10.1134/s1070363211060041

  日期：2011.6

  interaction of hydrophosphoryl compounds previously synthesized with biscarbamates in acetic anhydride and other solvents, the influence of the structure of phosphorus component and biscarbamate, and the effect of acid catalysis on the course of this two-component reaction. A new version of the mechanism of the three-component reaction of amidoalkylation of hydrophosphoryl compounds is suggested: it is regarded

  作为构建假α，α′-二肽分子的α-氨基磷酰基片段的简便方法，开发了一种新的温和的氢化磷酰基化合物在乙酸酐和乙酰氯混合物中的酰胺基烷基化的方法。反应中间体N，N′-亚苄基-和N，N检测，分离和鉴定了'-亚烷基双氨基甲酸酯。该报告提供了以下结果：研究了先前与双氨基甲酸酯合成的氢磷酰基化合物在乙酸酐和其他溶剂中的直接相互作用，磷组分和双甲酸氨基甲酸酯的结构的影响以及酸催化对该双组分反应过程的影响。 。提出了氢磷酰基化合物酰胺烷基烷基化三组分反应机理的新形式：它被认为是一个多阶段过程，涉及到双甲氨基甲酸酯的形成阶段，然后是Arbuzov型反应阶段，中间形成酰基亚胺基阳离子和具有三价磷的P-OAc衍生物。
• A general method for the synthesis of N-protected α-aminoalkylphosphinic acids
  作者：Shoujun Chen、James K. Cowark

  DOI：10.1016/0040-4039(96)00839-8

  日期：1996.6

  A general and highly convenient method for the synthesis of N-protected α-aminophosphinic acids, suitable for side chain elongation either from N-, P-, or C- termini to form a variety of phosphinic peptides, has been developed. The desired phosphinic acids were obtained in moderate to satisfactory yield by a three-component condensation reaction of benzyl carbamate, an aldehyde, and an alkylphosphonous

  已经开发了一种合成N-保护的α-氨基次膦酸的通用且高度方便的方法，该方法适于从N-，P-或C-末端侧链延伸以形成多种次膦酸肽。在非常温和的条件下，通过氨基甲酸苄酯，醛和烷基亚膦酸（或其金刚烷胺​​盐）的三组分缩合反应，可以以中等至令人满意的收率获得所需的次膦酸。
• Arbuzov-type reaction of acylphosphonites and N-alkoxycarbonylimine cations generated in situ with trifluoroacetic anhydride
  作者：Maxim E. Dmitriev、Valery V. Ragulin

  DOI：10.1016/j.tetlet.2012.01.094

  日期：2012.3

  N-protected α-aminoalkylphosphinic acids by the reaction of N,N′-benzylidene- or N,N′-alkylidenebiscarbamates, trifluoroacetic anhydride and the corresponding alkylphosphonous acids in methylene chloride or toluene is described. The results obtained confirm the earlier proposed mechanism for amidoalkylation of hydrophosphorylic compounds involving an Arbuzov-type reaction step.

  描述了通过N，N'-亚苄基-或N，N'-亚烷基双氨基甲酸酯，三氟乙酸酐和相应的烷基亚膦酸在二氯甲烷或甲苯中反应合成N-保护的α-氨基烷基次膦酸的温和方法。获得的结果证实了较早提出的涉及Arbuzov型反应步骤的氢磷酸化合物酰胺烷基化的机理。
• High-performance liquid chromatographic enantiomer separation and determination of absolute configurations of phosphinic acid analogues of dipeptides and their α-aminophosphinic acid precursors
  作者：Michael Lämmerhofer、Dieter Hebenstreit、Elena Gavioli、Wolfgang Lindner、Artur Mucha、Paweł Kafarski、Piotr Wieczorek

  DOI：10.1016/s0957-4166(03)00537-8

  日期：2003.9

  The enantiomers of N-benzyloxycarbonyl-phospinic pseudodipeptides and their N-benzyloxycarbonyl-alpha-aminophosphinic acid precursors as well as various other structural analogues were separated oil a set of cinchona alkaloid-derived chiral anion-exchangers by HPLC in the reversed-phase mode. Semi-preparative scale chromatography provided single enantiomers in 100 mg quantities. The configurations of the enantiomers were assigned indirectly by enantioselective chromatography on the basis of the elution order and was confirmed by enantiomeric reference compounds. (C) 2003 Elsevier Ltd. All rights reserved.